Oxidative C-O Cross‐Coupling of 1,3‐Dicarbonyl Compounds and Their Heteroanalogues with N‐Substituted Hydroxamic Acids and N‐Hydroxyimides

Oxidative C-O Cross‐Coupling of 1,3‐Dicarbonyl Compounds and Their Heteroanalogues with N‐Substituted Hydroxamic Acids and N‐Hydroxyimides Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2013, Volume: 355, Number: 11-12, Pages: 2375-2390 Pages count : 16 DOI: 10.1002/adsc.201300341

Authors

Terent'ev Alexander O. ¹ , Krylov Igor B. ¹ , Timofeev Vladimir P. ² , Starikova Zoya A. ³ , Merkulova Valentina M. ¹ , Ilovaisky Alexey I. ¹ , Nikishin Gennady I. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, Russian Federation, Fax: (+7)-499-135-5328
2	V. A. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilova st., 119991 Moscow, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova st., 119991 Moscow, Russian Federation

The oxidative CO cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues, 2-substituted malononitriles and cyanoacetic esters, with N-substituted hydroxamic acids and N-hydroxyimides was realized. The best results were obtained with the use of manganese(III) acetate [Mn(OAc)3] or the cobalt(II) acetate catalyst [Co(OAc)2cat.]/potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30–94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N-substituted hydroxamic acids and N-hydroxyimides.

Terent'ev A.O. , Krylov I.B. , Timofeev V.P. , Starikova Z.A. , Merkulova V.M. , Ilovaisky A.I. , Nikishin G.I.
Oxidative C-O Cross‐Coupling of 1,3‐Dicarbonyl Compounds and Their Heteroanalogues with N‐Substituted Hydroxamic Acids and N‐Hydroxyimides
Advanced Synthesis & Catalysis. 2013. V.355. N11-12. P.2375-2390. DOI: 10.1002/adsc.201300341 WOS Scopus OpenAlex

Web of science:	WOS:000327799600033
Scopus:	2-s2.0-84884500418
OpenAlex:	W1992986182

DB	Citing
OpenAlex	49
Scopus	46
Web of science	46